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1,3-Oxazole-4-carbonyl chloride → N-[6-(3-{[3-(1-cyano-1-methylethyl)benzoyl]amino}-4-methylphenoxy)-1,3-benzothiazol-2-yl]-1,3-oxazole-4-carboxamide

HRID 2190382
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2190382
[O:1]1[CH:5]=[C:4]([C:6](Cl)=[O:7])[N:3]=[CH:2]1.[NH2:9][C:10]1[S:11][C:12]2[CH:18]=[C:17]([O:19][C:20]3[CH:21]=[CH:22][C:23]([CH3:40])=[C:24]([NH:26][C:27](=[O:39])[C:28]4[CH:33]=[CH:32][CH:31]=[C:30]([C:34]([C:37]#[N:38])([CH3:36])[CH3:35])[CH:29]=4)[CH:25]=3)[CH:16]=[CH:15][C:13]=2[N:14]=1>N1C=CC=CC=1>[C:37]([C:34]([C:30]1[CH:29]=[C:28]([CH:33]=[CH:32][CH:31]=1)[C:27]([NH:26][C:24]1[CH:25]=[C:20]([CH:21]=[CH:22][C:23]=1[CH3:40])[O:19][C:17]1[CH:16]=[CH:15][C:13]2[N:14]=[C:10]([NH:9][C:6]([C:4]3[N:3]=[CH:2][O:1][CH:5]=3)=[O:7])[S:11][C:12]=2[CH:18]=1)=[O:39])([CH3:36])[CH3:35])#[N:38]
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Komponenten

4

Edukt 2

HCID 142814311,3-Oxazole-4-carbonyl chlorideHCID 86646002N-{5-[(2-amino-1,3-benzothiazol-6-yl)oxy]-2-methylphenyl}-3-(1-cyano-1-methylethyl)benzamide

Produkt 1

HCID 86655358N-[6-(3-{[3-(1-cyano-1-methylethyl)benzoyl]amino}-4-methylphenoxy)-1,3-benzothiazol-2-yl]-1,3-oxazole-4-carboxamideAusbeute 29 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

1,3-Oxazole-4-carbonyl chloride synthesized above was suspended in pyridine (4.0 mL) at 0° C., N-{5-[(2-amino-1,3-benzothiazol-6-yl)oxy]-2-methylphenyl}-3-(1-cyano-1-methylethyl)benzamide (200 mg, 0.452 mmol) produced in Example A7(vi) was added, and the mixture was stirred at room temperature for 12 hr. The reaction mixture was concentrated under reduced pressure, and the residue was suspended in methanol (4.0 mL). 1N Aqueous sodium hydroxide solution (4.0 mL) was added, and the mixture was stirred at room temperature for 30 min. To the reaction mixture was added 1N hydrochloric acid (10 mL), and the mixture was extracted with ethyl acetate (100 mL). The organic layer was washed with 5% aqueous sodium hydrogencarbonate solution (50 mL) and saturated brine (50 mL), successively, and dried over anhydrous sodium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by basic silica gel column chromatography (hexane/ethyl acetate=70/30→0/100), and the obtained solution was concentrated under reduced pressure. The residue was triturated with ethyl acetate/diisopropyl ether to give the title compound (70 mg, 29%) as a colorless solid.

Aufarbeitung

  1. additionwas added
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. addition1N Aqueous sodium hydroxide solution (4.0 mL) was added
  4. stirringthe mixture was stirred at room temperature for 30 min
  5. additionTo the reaction mixture was added 1N hydrochloric acid (10 mL)
  6. extractionthe mixture was extracted with ethyl acetate (100 mL)
  7. washThe organic layer was washed with 5% aqueous sodium hydrogencarbonate solution (50 mL) and saturated brine (50 mL)
  8. dry with materialsuccessively, and dried over anhydrous sodium sulfate
  9. filtrationThe insoluble material was filtered off
  10. concentrationthe filtrate was concentrated under reduced pressure
  11. customThe obtained residue was purified by basic silica gel column chromatography (hexane/ethyl acetate=70/30→0/100)
  12. concentrationthe obtained solution was concentrated under reduced pressure
  13. customThe residue was triturated with ethyl acetate/diisopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-7e537da0ed1b4126a47ffb7832654b9f
Quelldatensatz
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08324395B2

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